ContaminantDB: Cucurbitacin B

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 00:46:25 UTC

Update Date

2016-11-09 01:18:46 UTC

Accession Number

CHEM028884

Identification

Common Name

Cucurbitacin B

Class

Small Molecule

Description

Cucurbitacin B is found in bitter gourd. Together wth other cucurbitacins, is responsible for the bitter taste and toxic properties of spoilt cucumber

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Amarin?	HMDB
Cucurbitacine (b)	HMDB
Datisca principle b	HMDB
Datiscn principle b	HMDB
(3E)-6-{4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetic acid	Generator

Chemical Formula

C₃₂H₄₆O₈

Average Molecular Mass

558.703 g/mol

Monoisotopic Mass

558.319 g/mol

CAS Registry Number

6199-67-3

IUPAC Name

(3E)-6-{4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

Traditional Name

cucurbitacin B

SMILES

CC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(CC(O)C(=O)C4(C)C)C3(C)C(=O)CC12C

InChI Identifier

InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+

InChI Key

IXQKXEUSCPEQRD-OUKQBFOZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cucurbitacins

Direct Parent

Cucurbitacins

Alternative Parents

Substituents

Cucurbitacin skeleton
Triterpenoid
22-oxosteroid
21-oxosteroid
20-hydroxysteroid
Steroid ester
3-oxo-delta-5-steroid
2-hydroxysteroid
Hydroxysteroid
3-oxosteroid
11-oxosteroid
Oxosteroid
16-hydroxysteroid
Delta-5-steroid
Acyloin
Acryloyl-group
Alpha,beta-unsaturated ketone
Cyclic alcohol
Alpha-hydroxy ketone
Tertiary alcohol
Enone
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0056 g/L	ALOGPS
logP	3.7	ALOGPS
logP	3.13	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	12.8	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	138.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	151.04 m³·mol⁻¹	ChemAxon
Polarizability	60.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gvn-2204590000-999244d691afface476f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01b9-3102195000-67590cd44207aca4c298	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Cucurbitacin B,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_8) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052f-0002490000-340cd111be87d04d2109	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000w-1304920000-962e19bce41b3a8d95b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000l-2129410000-7ddb916021a8e5112d5a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4j-3900380000-17ed96fef5434e9fdd14	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4j-5903120000-0a58b6b4a29153fefb70	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9105300000-aed0a8da08a2f614aacc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000910000-2fb757c84672eba50afa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-adc51a9625e7766250c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4v-4001900000-b913bef2cb75f8c0debc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0100910000-d57bb7e6e5b6c7259024	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000e-9501410000-a5aebb06a3552f6953f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9612300000-18db14fe4f5cfcf5b1fa	Spectrum